Hotels with a Pool in Chestertown
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Hotels with a Pool in Chestertown
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown2.5 star property
Chestertown
- Pool loungers
8.6 out of 10, Excellent, (937 reviews)
8.6/10
Excellent
(937 reviews)
Pool perfection awaits from June to September at this pristine hotel. Travelers adore the sun-drenched seasonal pool with loungers for lazy afternoons. After swimming, visitors appreciate the fitness center, full breakfast, and spotlessly clean rooms.
Pool perfection awaits from June to September at this pristine hotel. Travelers adore the sun-drenched seasonal pool with loungers for lazy afternoons. After swimming, visitors appreciate the fitness center, full breakfast, and spotlessly clean rooms.
The price is $107
$107
$119 total
includes taxes & fees
Aug 19 - Aug 20
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing3.0 star property
Chestertown
- Pool loungers
- Private beach access
7.8 out of 10, Good, (93 reviews)
7.8/10
Good
(93 reviews)
Seasonal swimming awaits with pool umbrellas and loungers providing perfect relaxation after golf rounds or beach volleyball matches. Complete days with meals at Fairlee's restaurant and sunset gatherings around the firepit.
Seasonal swimming awaits with pool umbrellas and loungers providing perfect relaxation after golf rounds or beach volleyball matches. Complete days with meals at Fairlee's restaurant and sunset gatherings around the firepit.
The price is $147
$147
$168 total
includes taxes & fees
Jul 23 - Jul 24
Inn at Huntingfield Creek
Inn at Huntingfield Creek3.5 star property
Rock Hall
- Outdoor pool
- Pool loungers
- Full-service spa
10.0 out of 10, Exceptional, (68 reviews)
10/10
Exceptional
(68 reviews)
Poolside paradise unfolds at this waterfront bed & breakfast, where sun loungers invite leisurely days between spa massages. Egyptian cotton sheets and memory foam beds ensure rejuvenation after biking along nearby trails.
Poolside paradise unfolds at this waterfront bed & breakfast, where sun loungers invite leisurely days between spa massages. Egyptian cotton sheets and memory foam beds ensure rejuvenation after biking along nearby trails.
The price is $200
$200
$223 total
includes taxes & fees
Jul 23 - Jul 24
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn2.5 star property
Grasonville
- Indoor pool
- Hot tub
8.0 out of 10, Very Good, (1,000 reviews)
8.0/10
Very Good
(1,000 reviews)
Glide through crystal-clear waters in the refreshing indoor pool before melting away tension in the bubbling hot tub. Fitness enthusiasts appreciate the on-site sauna and gym while hikers enjoy nearby trails. Comfortable rooms complete the perfect getaway.
Glide through crystal-clear waters in the refreshing indoor pool before melting away tension in the bubbling hot tub. Fitness enthusiasts appreciate the on-site sauna and gym while hikers enjoy nearby trails. Comfortable rooms complete the perfect getaway.
The price is $98
$98
$109 total
includes taxes & fees
Jul 30 - Jul 31
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG2.5 star property
Grasonville
- Pool loungers
9.2 out of 10, Wonderful, (1,001 reviews)
9.2/10
Wonderful
(1,001 reviews)
Sparkling pool waters invite lazy afternoons under umbrellas with Chesapeake Bay vistas just beyond. Pristine rooms, delicious breakfast options, and hiking trails complete this waterfront escape where scenic beauty meets comfort.
Sparkling pool waters invite lazy afternoons under umbrellas with Chesapeake Bay vistas just beyond. Pristine rooms, delicious breakfast options, and hiking trails complete this waterfront escape where scenic beauty meets comfort.
The price is $100
$100
$111 total
includes taxes & fees
Aug 10 - Aug 11
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island2.5 star property
Grasonville
- Pool
- Free parking
- Free WiFi
- Air conditioning
- 24/7 front desk
7.8 out of 10, Good, (940 reviews)
7.8/10
Good
(940 reviews)
Crystal-clear waters beckon at the seasonal outdoor pool, available around the clock from May through October. Comfortable rooms await after exploring Queenstown Harbor Golf Links, while helpful staff earn consistent praise for making every stay exceptional.
Crystal-clear waters beckon at the seasonal outdoor pool, available around the clock from May through October. Comfortable rooms await after exploring Queenstown Harbor Golf Links, while helpful staff earn consistent praise for making every stay exceptional.
The price is $100
$100
$111 total
includes taxes & fees
Aug 10 - Aug 11
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD3.0 star property
Bel Air
- Pool umbrellas
8.8 out of 10, Excellent, (1,007 reviews)
8.8/10
Excellent
(1,007 reviews)
Poolside relaxation awaits beneath umbrella-dotted surroundings at the seasonal outdoor oasis. After swimming, guests appreciate the spotlessly clean rooms with premium bedding and the consistently praised complimentary breakfast.
Poolside relaxation awaits beneath umbrella-dotted surroundings at the seasonal outdoor oasis. After swimming, guests appreciate the spotlessly clean rooms with premium bedding and the consistently praised complimentary breakfast.
The price is $95
$95
$107 total
includes taxes & fees
Jul 28 - Jul 29
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MD3.0 star property
Aberdeen
- Indoor pool
8.8 out of 10, Excellent, (391 reviews)
8.8/10
Excellent
(391 reviews)
Swimmers dive into vacation bliss at the pristine indoor pool, available from morning until night. After invigorating laps, guests enjoy complimentary breakfast buffet before retreating to spacious rooms featuring kitchens and sofa beds.
Swimmers dive into vacation bliss at the pristine indoor pool, available from morning until night. After invigorating laps, guests enjoy complimentary breakfast buffet before retreating to spacious rooms featuring kitchens and sofa beds.
The price is $98
$98
$109 total
includes taxes & fees
Jul 30 - Jul 31
8.6 out of 10, Excellent, (665 reviews)
8.6/10
Excellent
(665 reviews)
Sparkling indoor pool welcomes swimmers with crystal-clear waters from 5 AM to 10 PM daily. Kids love the perfect-sized swimming area while adults appreciate the clean whirlpool after visiting the adjacent fitness center.
Sparkling indoor pool welcomes swimmers with crystal-clear waters from 5 AM to 10 PM daily. Kids love the perfect-sized swimming area while adults appreciate the clean whirlpool after visiting the adjacent fitness center.
The price is $110
$110
$123 total
includes taxes & fees
Jul 30 - Jul 31
Holiday Inn Belcamp - Aberdeen Area by IHG
Holiday Inn Belcamp - Aberdeen Area by IHG3.0 star property
Belcamp
- Indoor pool
8.4 out of 10, Very Good, (799 reviews)
8.4/10
Very Good
(799 reviews)
Dive into the warm, welcoming indoor pool at this spotlessly clean hotel after hiking nearby trails. A fitness center, arcade room, and the highly praised on-site restaurant with delicious breakfast create a perfect family retreat.
Dive into the warm, welcoming indoor pool at this spotlessly clean hotel after hiking nearby trails. A fitness center, arcade room, and the highly praised on-site restaurant with delicious breakfast create a perfect family retreat.
The price is $79
$79
$89 total
includes taxes & fees
Aug 2 - Aug 3
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina3.0 star property
Grasonville
- Indoor pool
- Pool loungers
9.4 out of 10, Exceptional, (791 reviews)
9.4/10
Exceptional
(791 reviews)
Pool enthusiasts discover a rejuvenating oasis at the indoor swimming sanctuary, complete with comfortable loungers for post-swim relaxation. Waterfront vistas, clean spacious rooms, and a fantastic 24-hour fitness center create the perfect island retreat.
Pool enthusiasts discover a rejuvenating oasis at the indoor swimming sanctuary, complete with comfortable loungers for post-swim relaxation. Waterfront vistas, clean spacious rooms, and a fantastic 24-hour fitness center create the perfect island retreat.
The price is $169
$169
$188 total
includes taxes & fees
Jul 29 - Jul 30
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area3.0 star property
Edgewood
- Indoor pool
7.0 out of 10, Good, (1,009 reviews)
7.0/10
Good
(1,009 reviews)
Aquatic bliss beckons at the temperature-controlled indoor pool, open daily from morning until evening. Guests appreciate the peaceful atmosphere throughout this immaculately maintained hotel, with exceptionally friendly staff always ready to assist.
Aquatic bliss beckons at the temperature-controlled indoor pool, open daily from morning until evening. Guests appreciate the peaceful atmosphere throughout this immaculately maintained hotel, with exceptionally friendly staff always ready to assist.
The price is $62
$62
$69 total
includes taxes & fees
Aug 2 - Aug 3
Ramada Hotel & Conference Center by Wyndham Edgewood
Ramada Hotel & Conference Center by Wyndham Edgewood2.0 star property
Edgewood
- Pool loungers
6.6 out of 10, (555 reviews)
6.6/10
(555 reviews)
Poolside paradise awaits with sun loungers and umbrellas surrounding the seasonal outdoor pool. Friendly staff ensure a carefree experience, while a fitness center, continental breakfast, and business amenities complete this rejuvenating retreat.
Poolside paradise awaits with sun loungers and umbrellas surrounding the seasonal outdoor pool. Friendly staff ensure a carefree experience, while a fitness center, continental breakfast, and business amenities complete this rejuvenating retreat.
The price is $74
$74
$83 total
includes taxes & fees
Jul 23 - Jul 24
Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott Middletown3.0 star property
Middletown
- Indoor pool
9.2 out of 10, Wonderful, (410 reviews)
9.2/10
Wonderful
(410 reviews)
Swimming enthusiasts cherish the inviting indoor pool, offering a serene escape regardless of weather. Located near numerous restaurants with convenient dining options, this hotel wins praise for its exceptionally friendly staff and spotless facilities.
Swimming enthusiasts cherish the inviting indoor pool, offering a serene escape regardless of weather. Located near numerous restaurants with convenient dining options, this hotel wins praise for its exceptionally friendly staff and spotless facilities.
The price is $119
$119
$132 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG2.5 star property
Edgewood
- Pool
- Free breakfast
- Free parking
- Free WiFi
- Connecting rooms available
- Air conditioning
9.0 out of 10, Wonderful, (620 reviews)
9.0/10
Wonderful
(620 reviews)
Sparkling waters welcome weary travelers at this spotless hotel's refreshing pool area. Just off I-95 near Cedar Lane Regional Park, guests praise the comfortable beds, exceptional staff service, and complimentary continental breakfast.
Sparkling waters welcome weary travelers at this spotless hotel's refreshing pool area. Just off I-95 near Cedar Lane Regional Park, guests praise the comfortable beds, exceptional staff service, and complimentary continental breakfast.
The price is $93
$93
$104 total
includes taxes & fees
Jul 26 - Jul 27
Candlewood Suites Aberdeen-Bel Air by IHG
Candlewood Suites Aberdeen-Bel Air by IHG2.5 star property
Bel Air
- Pool loungers
8.0 out of 10, Very Good, (520 reviews)
8.0/10
Very Good
(520 reviews)
Pool enthusiasts cherish the seasonal outdoor oasis, featuring comfortable sun loungers and umbrellas from May through September. Fully-equipped kitchenettes, a modern fitness center, and exceptionally clean accommodations create the perfect summer retreat.
Pool enthusiasts cherish the seasonal outdoor oasis, featuring comfortable sun loungers and umbrellas from May through September. Fully-equipped kitchenettes, a modern fitness center, and exceptionally clean accommodations create the perfect summer retreat.
The price is $76
$76
$85 total
includes taxes & fees
Jul 26 - Jul 27
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/Aberdeen2.5 star property
Aberdeen
- Indoor pool
9.0 out of 10, Wonderful, (676 reviews)
9.0/10
Wonderful
(676 reviews)
Splash into crystal-clear waters at the inviting indoor pool, where families can enjoy supervised swimming. Comfortable rooms, friendly staff, and a complimentary breakfast buffet complete this serene getaway with tennis courts and fitness center access.
Splash into crystal-clear waters at the inviting indoor pool, where families can enjoy supervised swimming. Comfortable rooms, friendly staff, and a complimentary breakfast buffet complete this serene getaway with tennis courts and fitness center access.
The price is $94
$94
$106 total
includes taxes & fees
Aug 2 - Aug 3
Homewood Suites by Hilton Bel Air
Homewood Suites by Hilton Bel Air3.0 star property
Bel Air
- Indoor pool
8.8 out of 10, Excellent, (503 reviews)
8.8/10
Excellent
(503 reviews)
Aquatic adventures begin in the temperature-controlled indoor pool, open daily from 10 AM to 7 PM. After swimming, guests explore nearby hiking trails or challenge themselves at local rock climbing spots, returning to comfortable rooms with full kitchens.
Aquatic adventures begin in the temperature-controlled indoor pool, open daily from 10 AM to 7 PM. After swimming, guests explore nearby hiking trails or challenge themselves at local rock climbing spots, returning to comfortable rooms with full kitchens.
The price is $106
$106
$118 total
includes taxes & fees
Aug 9 - Aug 10
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina3.0 star property
Grasonville
- Indoor pool
- Pool loungers
9.0 out of 10, Wonderful, (1,001 reviews)
9.0/10
Wonderful
(1,001 reviews)
Pool loungers surround the inviting indoor pool, creating a serene sanctuary after exploring waterfront activities. Spacious rooms with stunning balcony views complement the hotel's convenient marina location, just steps from dining options.
Pool loungers surround the inviting indoor pool, creating a serene sanctuary after exploring waterfront activities. Spacious rooms with stunning balcony views complement the hotel's convenient marina location, just steps from dining options.
The price is $147
$147
$163 total
includes taxes & fees
Aug 2 - Aug 3
La Quinta Inn & Suites by Wyndham Aberdeen-APG
La Quinta Inn & Suites by Wyndham Aberdeen-APG3.0 star property
Aberdeen
- Pool
- Free breakfast
- Pet friendly
- Free parking
- Free WiFi
- Connecting rooms available
9.0 out of 10, Wonderful, (1,007 reviews)
9.0/10
Wonderful
(1,007 reviews)
Poolside relaxation meets fitness enthusiasts at this immaculate hotel, featuring a seasonal outdoor oasis and fully-equipped gym. Clean rooms with laptop-friendly workspaces complete the experience, creating the perfect base for both leisure and business travelers.
Poolside relaxation meets fitness enthusiasts at this immaculate hotel, featuring a seasonal outdoor oasis and fully-equipped gym. Clean rooms with laptop-friendly workspaces complete the experience, creating the perfect base for both leisure and business travelers.
The price is $88
$88
$99 total
includes taxes & fees
Aug 2 - Aug 3
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top landmarks in Chestertown
Garfield Center for the Arts at the Prince Theater
6.8/10 (5 reviews)
Why not give yourself a treat with a trip to Garfield Center for the Arts at the Prince Theater, one of the family attractions located 0.7 mi (1.2 km) from central Chestertown. If you have fun at Garfield Center for the Arts at the Prince Theater, you'll love Larrabee Arts Center, located nearby.
Historical Society of Kent County Maryland
7.4/10 (6 reviews)
Historical Society of Kent County Maryland is 0.7 mi (1.2 km) from central Chestertown, why not stop by during your stay. If you want to experience more of the culture Chestertown has to offer, head to Garfield Center for the Arts at the Prince Theater, Chestertown Historic District, and River Arts Chestertown.